Why is it some monks (Yuttadhammo specifically) walks barefoot in his alms rounds as well as while doing walking meditation?
Is there a purpose to it?
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Good householder, Monks, who follow the Buddha, don't wear shoes generally. If they make exceptions accourding to allowances by the Buddha to wear on rocky roads, in their mnastery (to keep the floor of buildings clean) or if foot sickness, and some other, they (inmost cases) are to bag them bag some meters before a settlement. Almsround is a case where less allowances to wear world fit. (Details see under footware here )
"One should not enter a village while wearing leather footwear. Whoever should enter: an offense of wrong doing." ... "I allow that an ill bhikkhu enter a village while wearing leather footwear." — Mv.V.12
and so on...
On why a "beggar" does not wear shoes should be general clear, a matter of humble and modesty of a simple live, at least on alms and a matter of respect and staying mindful, not turning the eyes orher than some meters before one on the ground. People generally are used to put off the shoes when enter others homes...
The way of a Buddhas disciple: Bhante makes that very exemplary, at least to be seen on alms in Sri Lanka on video.
As a bee — without harming the blossom, its color, its fragrance — takes its nectar & flies away: so should the sage go through a village.
*and it's dhp-story
Btw., it's good and a sign of respect, to put of ones shoes as well and try to settle oneself a little lower so that ones almsgiving is a higher and dedicated for upwardly and beyound.
A more refined possibility to step forward to understand, might be to step on this without taking ones shoes inbetween the reality of effects of touch.
(Note: this is not given for stacks exchange and trade or commercial purpose, binding in this wheel of bonds, but for liberation from it.)
Barefoot used to be normal -- and wearing shoes was disrespectful and/or a sign of feeling superior.
The Vinaya used to explicitly allow footwear in outlying areas -- and not in public.
Lay society has changed, so wearing shoes is now seen as polite, and the custom has adapted accordingly -- i.e. you might see monks with footwear now - similarly there are times and places where the climate isn't appropriate for bare feet.
But I don't think of bare feet as remarkable. I used to walk barefoot as a teen (not for those same reasons), obviously enough it's feasible.
In ancient India , most of sages used to walk barefoot like tirthankar jains , buddha , their best students. Walking barefoot was also among poor locals. Nowdays too , few forest tribals of North-East India , Chhattisgarh & M.P. live barefoot.
Among sages , barefoot living was an indication to :
Simple life (like common man)
Vairagya (no interest in pleasures)
Energy tranfer occurs through foot
To not kill small beings ,even unwillingly(slight chance) cause barefoot increases sensations.
Truth-Seeker has stopped too much travelling and gone forth for deep meditation within a small area.
Moreover ,as Meditator becomes strong in meditation , tendency towards barefoot increases, without any enforcement of sheel(Vinaya) .
It is also very practical because one needs not dry out shoes or socks, going barefoot or wearing sandals of some kind solves this. The staying dry comes into play a lot as it gets cold andor wet, it takes a lot of maintenance and winter shoes are weighty.
Afaik people can comfortably walk thus partially exposed to cold even in low temperatures like -20C but it requires some conditioning.
Basically It solves the problem of having more requisites than one can carry, in particular the 2-3 pairs of footwear & socks. One is saving ~3kg of weight there which is a lot considering that it's probably going to make up for ~20% of the total weight of requisites which can be comfortably carried.
benefits of walking barefoot, some scientific study (small study) https://www.google.com/books/edition/Earthing/DtQVwPcBrr4C?hl=en&gbpv=1&printsec=frontcover
edit: (this was too long to add as a comment) To the people who downvoted my answer, You should add an explanatory comment to explain why so everyone can understand why they should be avoiding the type of answer I gave. This anonymous downvoting creates a culture of distrust and discourages experts from responding because they're trying to protect their 'reputation' and 'credit rating'. Now my answer has nothing to do with Buddhism, which is why I assume it was downvoted. But I qualified my answer stating it was so, and I have no affiliation with the author of the book, I simply found it to be very useful and interesting and worth sharing. So go ahead and keep downvoting me people, I'm going to share what I feel to be useful information whenever it's relevant, I care not about your opinion of me and your reputation badges and what not.